We hit the road early from Cleveland, packed lunches in the car, and made the five-hour drive to Hershey as part of our road trip to Williamsburg. We planned the journey with a half day in Hershey, PA and a half day in Gettysburg, PA, which turned out to be the perfect way to break up the drive. Because what better way to kick off a family winter break road trip than in Chocolate Town, U.S.A.? The drive flew by with tablets, snacks for the kids, and plenty of anticipation for the sweet adventures ahead.
First Stop: The Hershey Story Museum
Our first stop was the Hershey Story Museum, a perfect place to dive into the history of Milton Hershey and his chocolate empire. The museum is super interactive, and the kids were captivated by the hands-on exhibits. From wrapping chocolate bars to learning about the town’s history, there was something for every age. We spent about an hour and a half wandering through the museum, soaking in the stories and snapping plenty of photos.
Tip: The museum is less crowded early in the day, so hitting it first thing can make your visit smoother, especially with kids.

Next Up: Hershey’s Chocolate World
After the museum, it was time for the main attraction—Hershey’s Chocolate World. The factory area is free to explore and even offers a complimentary 30-minute ride tour that shows how chocolate is made. We decided to skip the longer 45-minute wait for the ride (Pro Tip: go first thing in the morning or later in the evening for shorter lines) and instead wandered through the Hershey Store.
Walking into the store is like stepping into a candy wonderland. There are free exhibits, fun chocolate displays, and endless Hershey souvenirs. From giant chocolate bars to adorable plush Hershey Kisses, it’s impossible to leave empty-handed. Naturally, we grabbed a bag of treats for the road—because a family road trip without chocolate is just a car ride.




Dinner & Relaxation: Troegs Independent Brewing
We wrapped up our Hershey stop with dinner at Troegs Independent Brewing, a true gem for families and beer lovers alike. The menu had something for everyone—craft beers for the adults, hearty options for kids, and a relaxed, welcoming vibe that made winding down after a full day a pleasure. By the time we left, everyone was satisfied and ready for the drive back, already dreaming of our next Hershey adventure.

Quick Tips for a Half-Day Hershey Winter Trip
- Start Early: Hershey Story Museum and Chocolate World are less crowded in the morning.
- Pack Snacks: Hershey is sweet, but car snacks are still essential for a long road trip.
- Plan Your Ride Time: Skip longer lines at Chocolate World by timing your ride strategically.
- Dress Warm: It is cold in winter in PA!
- Leave Room for Souvenirs: The Hershey store is a candy-lover’s paradise.
Whether you’re a chocolate fanatic, history buff, or just looking for a family-friendly winter getaway, Hershey, PA delivers a perfectly sweet half-day escape.
👉 Looking for more ideas? Click here for family-friendly road trips from Cleveland, including weekend and winter getaways
